Five key lessons learned from five years working remotely

This year marks five yearsworkingremotely for me. After spending the previous decade working in a traditional office environment, I’ve learned what helps make distributed teams work well—and some of their shortcomings as well.

Given my experience, I’ve had the opportunity to chat with a few people on the topic of distributed design teams recently. Most questions surround the topic of getting started and how to make sure remote team members feel included with the team.

Working remotely is different. It’s forces organizations to move from an oral culture (i.e. “Hey let’s just hop in a conference room and talk about X for 30 minutes”) to a written culture (i.e. “Let me document my thoughts and share with the team so we can discuss it”). This is a natural, growing step for most organizations. Organizations typically make this transition when grow beyond 50 people and becomes more pronounced the bigger the organization gets. As organizations expand within a location or add office locations, it becomes harder to communicate orally.

Instead organizations need to move to a written culture, creating historical artifacts for others that help document the purpose, focus, and scope of decisions. These artifacts can then be revisited weeks, months, and even years later to provide needed context for those who had forgotten why a decision was made or weren’t around at the time.

Remote teams are no different. By distributing your team, you are forcing your team to adopt a writing culture. However remote working also introduces some unique challenges. Unlike a new office location, remote team members are very much by themselves. They don’t have an office support staff or HR department close by. There aren’t any other co-workers physically near them. This can lead to remote workers feeling alone at times, which is why it’s crucial for organizations who want to hire remote team members to properly support them.

The more remote team members you add, the easier it becomes supporting them. While it may be hard initially, the pay-off is it allows you to expand the potential candidates you can add to your team and retain current team members who may have to move, but still want to work with you.

So if you’re considering hiring a remote team member, here are five keylessons I’ve learned working remote the last five years:

If one person is remote, everyone’s remote

For teams thinking about adding remote workers, the biggest thing I can stress is that adding remote team members changes how everyone works.

Far too often I hear stories of organizations who hired remote team members, but never properly changed how they worked to account for this new dynamic. It left everyone frustrated by the experience. Remote team members didn’t feel involved and non-remote team members didn’t have insight to what remote team members were doing.

Adding remote team members changes how everyone works.

At Stack Overflow, the company’s core philosophy for remote working is if one person is remote, everyone’s remote. But what does that mean? It means that no matter where you work, in an office or remotely, everyone approaches things the same way. It’s the only way remote teams are possible.

A few practical examples:

If you need to schedule a meeting, don’t hold it in a conference room. Instead everyone should join from their desk in a video hangout. Too often people joining a conference call remotely can feel left out or forgotten about in a conference room discussion. By having everyone join the same way, no one is at a disadvantage.

Product decisions aren’t decided on a whim over lunch or after-hours. Instead any discussions which may take place are documented and presented back to your team so everyone has the opportunity to review and provide feedback. This not only helps remote team members feel involved, but also helps them know that they could propose ideas in the same way and receive similar feedback.

Communicate via chat first before hoping in a call. Not only does this respect your co-workers time and priorities, but allows others to respond you may not have considered asking initially.

Even if you work in an office, these are simple things that you can start doing today to help remote team members feel included.

Treat everyone the same way

When you’re a remote team member, it’s easy to feel left out. When you see office co-workers enjoying perks you’re unable to enjoy, that exasperates the feeling, making you feel unappreciated and as an after-thought.

To combat this, companies need to consider how they might include remote team members—even if they’re unable to be physically present. A few practical ways:

Does the company provide a working area, desk, office chair, computer equipment, and internet access for people in the office? Of course! Well, do the same thing for remote team members. Set them up for success by giving them tools they need to get the job done.

Is the company throwing a party? Great! Invite remote team members to join you if they’re close-by or allow them to expense their own party if they’re too far away.

Do you hand out new swag to team members? Make sure someone is sending it out to new team members as well.

These are some of the ways Stack Overflow makes sure remote team members feel like any other employee—whether they’re in the office or not.

Embrace flexibility but have overlap

One of the great things about working remotely at Stack Overflow is that you can work from anywhere and when you want. You don’t have to spend thousands of dollars and countless hours every year commuting into an office. Instead you choose where you want to work and when works best for you.

Having remote team members means you have to embrace being flexible. Maybe some team members will outside your time zone, work earlier hours, work later hours, or may have to take a 2–hour break in the middle of the day because of some personal items. That’s okay—as long as you communicate and still have have overlapping working hours.

At Stack Overflow, my product team is composed of 9 people, each working in a different area of the world: Brazil, Poland, London, Boston, New York City, Los Angeles, San Francisco, North Carolina, and Pennsylvania. That’s 9 different places spread across 9 hours! The only way we make it work is that we all share at least 3–4 hours every day during a normal 8am–5pm Eastern Time Zone (ET) workday.

When you have team members living in different time zones, it’s unlikely they’ll be able to share the exact same hours as you—and that’s fine. Just be sure to use the time you are working through outstanding items that require conversations when everyone’s available.

Communicate asynchronously

Hiring remote team members means everyone won’t be working at the same times. This means you can’t rely on having face-to-face conversations to relay information. Instead you need to write down your thoughts, questions, status, or roadblocks so team members can respond when they’re available.

Google Docs, Trello cards, chat messages, GitHub pull requests—use the tools your team already uses. Whether you’re remote or not, this is a great habit to get into regardless. It respects a co-worker’s time by allowing them to respond when they’re available—not when it’s top of mind for you.

This could introduce some lag, yet that lag can be kept to a minimum by setting short deadlines for responses and holding team members accountable. Video hangouts will still happen, but they’ll serve more as an opportunity to review and clarify.

Get together at key moments

When I worked in an office, I was interrupted (intentionally and unintentionally) regularly. As I worked on increasingly complex and difficult design problems, it became harder and harder to properly concentrate at the office. Instead I found I needed to work somewhere else or come in earlier before any else showed up.

By working from home, I now have the ability to concentrate every day without countless interruptions. Yet there are some office benefits I do miss: being able to more quickly build repertoire with co-workers and some tasks I’ve found are better done in person than remotely. For these reasons, it’s good for teams to schedule meet-ups to get together. There are a few different reasons to meet-up:

Company meet-ups: These exist as a way for the whole company or large departments to get together. By having the larger team together, you encourage interaction that you don’t normally have on a day-to-day basis. As a company you can celebrate successes, challenge each other for the coming year, and spend time getting to know each other.

Team meet-ups: With some much going on at company meet-ups, it’s hard to schedule large blocks of time to discuss more pressing issues for your immediate team. Invest in your team by scheduling a separate time to meet-up. During this time you can talk about more practical items that affect your team.

Product team meet-ups: A few times a year, product teams will need to conduct a few days of brainstorming. In these moments, it’s good to get key people together in one place and work together. While this can be done remotely, I’ve found it a frustrating experience because of the time zone differences. Instead of making a difficult process even tougher, schedule some time together in the same place.